Bergman Ylva E, Mulder Roger, Perlmutter Patrick
School of Chemistry, Monash University, PO Box 23, Victoria 3800, Australia.
J Org Chem. 2009 Mar 20;74(6):2589-91. doi: 10.1021/jo802623n.
The key tricyclic intermediate 3a, for the total synthesis of the C(20)-nor analogue of salvinorin A, was prepared in seven steps from 3-furaldehyde. Key steps involved a highly regio- and diastereoselective Lewis acid assisted Diels-Alder reaction followed by base-promoted epimerization and a completely stereoselective conjugate reduction.
用于全合成Salvinorin A的C(20)-去甲类似物的关键三环中间体3a,由3-糠醛经七步反应制备而成。关键步骤包括高度区域和非对映选择性的路易斯酸辅助狄尔斯-阿尔德反应,随后是碱促进的差向异构化以及完全立体选择性的共轭还原。